# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

data_cd-ljl-dqs-b-2
_audit_creation_date              2019-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C21 H20 O4'
_chemical_formula_sum             'C21 H20 O4'
_chemical_formula_weight          336.37
_chemical_absolute_configuration  ?
_chemical_melting_point           ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system       'orthorhombic'
_space_group_IT_number            29
_space_group_name_H-M_alt         'P c a 21'
_space_group_name_Hall            'P 2c -2ac'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x+1/2, -y, z'
 '-x+1/2, y, z+1/2'

_cell_length_a                    10.5308(10)
_cell_length_b                    18.5025(16)
_cell_length_c                    8.7370(7)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1702.4(3)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     1524
_cell_measurement_temperature     293.9(5)
_cell_measurement_theta_max       68.1020
_cell_measurement_theta_min       6.5370
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     0.732
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.16928
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             'clear light colourless'
_exptl_crystal_colour_lustre      clear
_exptl_crystal_colour_modifier    light
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.312
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        plate
_exptl_crystal_F_000              712
_exptl_crystal_size_max           0.5
_exptl_crystal_size_mid           0.3
_exptl_crystal_size_min           0.1
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0394
_diffrn_reflns_av_unetI/netI      0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_k_min        -22
_diffrn_reflns_limit_l_max        8
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_number             5135
_diffrn_reflns_point_group_measured_fraction_full 0.752
_diffrn_reflns_point_group_measured_fraction_max 0.731
_diffrn_reflns_theta_full         67.684
_diffrn_reflns_theta_max          71.763
_diffrn_reflns_theta_min          4.780
_diffrn_ambient_environment       air
_diffrn_ambient_temperature       293.9(5)
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  15.9595
_diffrn_detector_type             EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    4.37    --  -36.54  57.00 -60.00   84
  2  ω   -108.00  -7.00   1.00    4.37    --  -36.54 -19.00 -30.00  101
  3  ω      1.00  75.00   1.00    4.37    --   36.54 -99.00 150.00   74
  4  ω     38.00 124.00   1.00   17.48    --  106.21 -45.00-150.00   86
  5  ω     37.00 109.00   1.00   17.48    --  106.21 -94.00-180.00   72
  6  ω     85.00 176.00   1.00   17.48    --  106.21  30.00 120.00   91
  7  ω     37.00 109.00   1.00   17.48    --  106.21 -94.00 -30.00   72
  8  ω     88.00 169.00   1.00   17.48    --  106.21  61.00-150.00   81
;
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type   'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11       -0.0766335000
_diffrn_orient_matrix_UB_12       -0.0509032000
_diffrn_orient_matrix_UB_13       -0.0308021000
_diffrn_orient_matrix_UB_21       0.0323900000
_diffrn_orient_matrix_UB_22       -0.1183597000
_diffrn_orient_matrix_UB_23       -0.0780793000
_diffrn_orient_matrix_UB_31       0.0010987000
_diffrn_orient_matrix_UB_32       -0.0693899000
_diffrn_orient_matrix_UB_33       0.1551414000
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            CuK\a
_diffrn_radiation_wavelength      1.54184
_diffrn_source                    'fine-focus sealed X-ray tube'
_diffrn_source_type               'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage          0.388
_reflns_Friedel_fraction_full     0.465
_reflns_Friedel_fraction_max      0.441
_reflns_number_gt                 1831
_reflns_number_total              2438
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      66.97
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction         'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.604
_refine_diff_density_min          -0.293
_refine_diff_density_rms          0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 330 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.3(5)
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.043
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      226
_refine_ls_number_reflns          2438
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1008
_refine_ls_R_factor_gt            0.0879
_refine_ls_restrained_S_all       1.042
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1992P)²+0.0323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.2521
_refine_ls_wR_factor_ref          0.2838
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00J), C00K(H00K,H00L), C00L(H00M,H00N), C00O(H00Q,H00R), C00P(H00S,
 H00T)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00M(H00O), C00N(H00P)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O001 O 0.5172(4) 0.1969(2) 0.5076(6) 0.0822(11) Uani 1 1 d . . . . .
 O002 O 0.2953(5) 0.1260(2) 0.3657(6) 0.0927(14) Uani 1 1 d . . . . .
 O003 O 0.6027(6) 0.1324(3) 0.6942(7) 0.1068(18) Uani 1 1 d . . . . .
 O004 O 0.3527(7) 0.0469(3) 0.5436(8) 0.1149(19) Uani 1 1 d . . . . .
 C005 C 0.5954(6) 0.1455(3) 0.5585(10) 0.0833(18) Uani 1 1 d . . . . .
 C006 C 0.3651(8) 0.0723(3) 0.4201(9) 0.0882(17) Uani 1 1 d . . . . .
 C007 C 0.3519(5) 0.3526(4) 0.5308(7) 0.0763(14) Uani 1 1 d . . . . .
 C008 C 0.3345(6) 0.2726(4) 0.5356(7) 0.0810(15) Uani 1 1 d . . . . .
 C009 C 0.3757(5) 0.5060(4) 0.5315(7) 0.0757(13) Uani 1 1 d . . . . .
 C00A C 0.3835(5) 0.5856(4) 0.5363(8) 0.0802(15) Uani 1 1 d . . . . .
 C00B C 0.4514(8) 0.6204(5) 0.6521(10) 0.097(2) Uani 1 1 d . . . . .
 H00B H 0.4931 0.5931 0.7258 0.117 Uiso 1 1 calc R . . . .
 C00C C 0.4574(10) 0.6956(5) 0.6588(11) 0.110(3) Uani 1 1 d . . . . .
 H00C H 0.5036 0.7184 0.7356 0.132 Uiso 1 1 calc R . . . .
 C00D C 0.4526(8) 0.3866(4) 0.5956(12) 0.102(2) Uani 1 1 d . . . . .
 H00D H 0.5162 0.3588 0.6401 0.122 Uiso 1 1 calc R . . . .
 C00E C 0.2352(7) 0.2409(4) 0.4708(8) 0.0881(17) Uani 1 1 d . . . . .
 H00E H 0.1763 0.2706 0.4224 0.106 Uiso 1 1 calc R . . . .
 C00F C 0.2768(8) 0.4714(4) 0.4602(11) 0.102(2) Uani 1 1 d . . . . .
 H00F H 0.2157 0.4988 0.4099 0.122 Uiso 1 1 calc R . . . .
 C00G C 0.3945(7) 0.7354(4) 0.5506(12) 0.102(2) Uani 1 1 d . . . . .
 H00G H 0.3968 0.7856 0.5555 0.122 Uiso 1 1 calc R . . . .
 C00H C 0.4645(8) 0.4601(4) 0.5980(12) 0.103(2) Uani 1 1 d . . . . .
 H00H H 0.5348 0.4803 0.6461 0.124 Uiso 1 1 calc R . . . .
 C00I C 0.3231(7) 0.6284(4) 0.4288(10) 0.0898(18) Uani 1 1 d . . . . .
 H00I H 0.2780 0.6064 0.3501 0.108 Uiso 1 1 calc R . . . .
 C00J C 0.4652(11) 0.0494(5) 0.3067(12) 0.118(3) Uani 1 1 d . . . . .
 H00A H 0.4669 0.0844 0.2239 0.142 Uiso 1 1 calc R . . . .
 H00J H 0.4406 0.0033 0.2634 0.142 Uiso 1 1 calc R . . . .
 C00K C 0.4290(7) 0.2269(4) 0.6178(8) 0.0851(16) Uani 1 1 d . . . . .
 H00K H 0.4746 0.2559 0.6923 0.102 Uiso 1 1 calc R . . . .
 H00L H 0.3859 0.1882 0.6717 0.102 Uiso 1 1 calc R . . . .
 C00L C 0.6625(9) 0.1073(4) 0.4339(13) 0.108(2) Uani 1 1 d . . . . .
 H00M H 0.6743 0.1411 0.3501 0.129 Uiso 1 1 calc R . . . .
 H00N H 0.7461 0.0940 0.4708 0.129 Uiso 1 1 calc R . . . .
 C00M C 0.2649(8) 0.3968(4) 0.4608(11) 0.102(2) Uani 1 1 d . . . . .
 H00O H 0.1955 0.3759 0.4120 0.123 Uiso 1 1 calc R . . . .
 C00N C 0.3279(8) 0.7022(5) 0.4350(13) 0.107(2) Uani 1 1 d . . . . .
 H00P H 0.2864 0.7298 0.3614 0.129 Uiso 1 1 calc R . . . .
 C00O C 0.2101(8) 0.1607(5) 0.4693(10) 0.098(2) Uani 1 1 d . . . . .
 H00Q H 0.2215 0.1412 0.5714 0.117 Uiso 1 1 calc R . . . .
 H00R H 0.1231 0.1517 0.4380 0.117 Uiso 1 1 calc R . . . .
 C00P C 0.6015(12) 0.0423(7) 0.3728(18) 0.148(5) Uani 1 1 d . . . . .
 H00S H 0.5991 0.0065 0.4540 0.178 Uiso 1 1 calc R . . . .
 H00T H 0.6556 0.0232 0.2926 0.178 Uiso 1 1 calc R . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O001 C005 1.335(7) . ?
 O001 C00K 1.448(8) . ?
 O002 C006 1.324(9) . ?
 O002 C00O 1.428(10) . ?
 O003 C005 1.212(10) . ?
 O004 C006 1.184(10) . ?
 C005 C00L 1.478(12) . ?
 C006 C00J 1.507(14) . ?
 C007 C008 1.493(10) . ?
 C007 C00D 1.357(11) . ?
 C007 C00M 1.371(9) . ?
 C008 C00E 1.325(10) . ?
 C008 C00K 1.491(9) . ?
 C009 C00A 1.476(9) . ?
 C009 C00F 1.373(10) . ?
 C009 C00H 1.390(10) . ?
 C00A C00B 1.396(10) . ?
 C00A C00I 1.383(10) . ?
 C00B H00B 0.9300 . ?
 C00B C00C 1.393(13) . ?
 C00C H00C 0.9300 . ?
 C00C C00G 1.370(14) . ?
 C00D H00D 0.9300 . ?
 C00D C00H 1.366(11) . ?
 C00E H00E 0.9300 . ?
 C00E C00O 1.508(12) . ?
 C00F H00F 0.9300 . ?
 C00F C00M 1.386(11) . ?
 C00G H00G 0.9300 . ?
 C00G C00N 1.375(14) . ?
 C00H H00H 0.9300 . ?
 C00I H00I 0.9300 . ?
 C00I C00N 1.368(11) . ?
 C00J H00A 0.9700 . ?
 C00J H00J 0.9700 . ?
 C00J C00P 1.553(15) . ?
 C00K H00K 0.9700 . ?
 C00K H00L 0.9700 . ?
 C00L H00M 0.9700 . ?
 C00L H00N 0.9700 . ?
 C00L C00P 1.465(16) . ?
 C00M H00O 0.9300 . ?
 C00N H00P 0.9300 . ?
 C00O H00Q 0.9700 . ?
 C00O H00R 0.9700 . ?
 C00P H00S 0.9700 . ?
 C00P H00T 0.9700 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C005 O001 C00K 116.5(6) . . ?
 C006 O002 C00O 117.3(6) . . ?
 O001 C005 C00L 112.9(7) . . ?
 O003 C005 O001 120.5(7) . . ?
 O003 C005 C00L 126.5(7) . . ?
 O002 C006 C00J 111.2(7) . . ?
 O004 C006 O002 124.3(8) . . ?
 O004 C006 C00J 124.4(8) . . ?
 C00D C007 C008 123.0(5) . . ?
 C00D C007 C00M 115.6(6) . . ?
 C00M C007 C008 121.4(6) . . ?
 C00E C008 C007 121.5(6) . . ?
 C00E C008 C00K 118.8(6) . . ?
 C00K C008 C007 119.6(6) . . ?
 C00F C009 C00A 121.4(6) . . ?
 C00F C009 C00H 114.5(6) . . ?
 C00H C009 C00A 124.1(6) . . ?
 C00B C00A C009 120.6(6) . . ?
 C00I C00A C009 121.8(6) . . ?
 C00I C00A C00B 117.6(7) . . ?
 C00A C00B H00B 119.5 . . ?
 C00C C00B C00A 120.9(8) . . ?
 C00C C00B H00B 119.5 . . ?
 C00B C00C H00C 120.4 . . ?
 C00G C00C C00B 119.1(8) . . ?
 C00G C00C H00C 120.4 . . ?
 C007 C00D H00D 118.7 . . ?
 C007 C00D C00H 122.6(7) . . ?
 C00H C00D H00D 118.7 . . ?
 C008 C00E H00E 117.4 . . ?
 C008 C00E C00O 125.2(6) . . ?
 C00O C00E H00E 117.4 . . ?
 C009 C00F H00F 118.9 . . ?
 C009 C00F C00M 122.1(6) . . ?
 C00M C00F H00F 118.9 . . ?
 C00C C00G H00G 119.6 . . ?
 C00C C00G C00N 120.9(8) . . ?
 C00N C00G H00G 119.6 . . ?
 C009 C00H H00H 118.6 . . ?
 C00D C00H C009 122.7(7) . . ?
 C00D C00H H00H 118.6 . . ?
 C00A C00I H00I 119.1 . . ?
 C00N C00I C00A 121.9(8) . . ?
 C00N C00I H00I 119.1 . . ?
 C006 C00J H00A 108.5 . . ?
 C006 C00J H00J 108.5 . . ?
 C006 C00J C00P 115.2(8) . . ?
 H00A C00J H00J 107.5 . . ?
 C00P C00J H00A 108.5 . . ?
 C00P C00J H00J 108.5 . . ?
 O001 C00K C008 109.0(5) . . ?
 O001 C00K H00K 109.9 . . ?
 O001 C00K H00L 109.9 . . ?
 C008 C00K H00K 109.9 . . ?
 C008 C00K H00L 109.9 . . ?
 H00K C00K H00L 108.3 . . ?
 C005 C00L H00M 108.1 . . ?
 C005 C00L H00N 108.1 . . ?
 H00M C00L H00N 107.3 . . ?
 C00P C00L C005 116.8(9) . . ?
 C00P C00L H00M 108.1 . . ?
 C00P C00L H00N 108.1 . . ?
 C007 C00M C00F 122.3(7) . . ?
 C007 C00M H00O 118.8 . . ?
 C00F C00M H00O 118.8 . . ?
 C00G C00N H00P 120.2 . . ?
 C00I C00N C00G 119.6(9) . . ?
 C00I C00N H00P 120.2 . . ?
 O002 C00O C00E 109.8(6) . . ?
 O002 C00O H00Q 109.7 . . ?
 O002 C00O H00R 109.7 . . ?
 C00E C00O H00Q 109.7 . . ?
 C00E C00O H00R 109.7 . . ?
 H00Q C00O H00R 108.2 . . ?
 C00J C00P H00S 107.8 . . ?
 C00J C00P H00T 107.8 . . ?
 C00L C00P C00J 118.1(9) . . ?
 C00L C00P H00S 107.8 . . ?
 C00L C00P H00T 107.8 . . ?
 H00S C00P H00T 107.1 . . ?

_shelx_SHELXL_version_number      '2014/7'
_olex2_date_sample_data_collection 2019-11-12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.989
_oxdiff_exptl_absorpt_empirical_full_min 0.637
